US5036074A - Certain 2,4-dichloro-phenyl(loweralkylidene) pyridines having fungicidal activity - Google Patents
Certain 2,4-dichloro-phenyl(loweralkylidene) pyridines having fungicidal activity Download PDFInfo
- Publication number
- US5036074A US5036074A US07/481,264 US48126490A US5036074A US 5036074 A US5036074 A US 5036074A US 48126490 A US48126490 A US 48126490A US 5036074 A US5036074 A US 5036074A
- Authority
- US
- United States
- Prior art keywords
- dichloro
- pyridine
- methyl
- cyclopropyl
- methylenephenethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 11
- 150000003222 pyridines Chemical class 0.000 title abstract description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 239000002253 acid Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 16
- 241000233866 Fungi Species 0.000 claims abstract description 15
- 238000003898 horticulture Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 59
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- DSXSGCRDTSCUKG-UHFFFAOYSA-N 3-[2-(2,4-dichlorophenyl)hept-3-en-3-yl]pyridine Chemical compound C=1C=CN=CC=1C(=CCCC)C(C)C1=CC=C(Cl)C=C1Cl DSXSGCRDTSCUKG-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- YFSPOCGEJKDNON-UHFFFAOYSA-N 3-[1-[1-(2,4-dichlorophenyl)ethenyl]cyclopropyl]pyridine Chemical compound ClC1=CC(Cl)=CC=C1C(=C)C1(C=2C=NC=CC=2)CC1 YFSPOCGEJKDNON-UHFFFAOYSA-N 0.000 claims description 10
- SFKGHMTVZVVBIT-UHFFFAOYSA-N 3-[3-(2,4-dichlorophenyl)but-1-en-2-yl]pyridine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)C(=C)C1=CC=CN=C1 SFKGHMTVZVVBIT-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- JZZMADZMWUECJT-UHFFFAOYSA-N 3-[3-(2,4-dichlorophenyl)-1-methoxyhex-1-en-5-yn-2-yl]pyridine Chemical compound C=1C=CN=CC=1C(=COC)C(CC#C)C1=CC=C(Cl)C=C1Cl JZZMADZMWUECJT-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- 150000004699 copper complex Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- UTVCWWXWGGLMAK-UHFFFAOYSA-N 3-[1-[1-(2,4-dichlorophenyl)-2-methoxyethenyl]cyclopropyl]pyridine Chemical compound C1CC1(C=1C=NC=CC=1)C(=COC)C1=CC=C(Cl)C=C1Cl UTVCWWXWGGLMAK-UHFFFAOYSA-N 0.000 claims description 4
- WQRNMNNPLNYLFU-UHFFFAOYSA-N 3-[1-[1-(2,4-dichlorophenyl)ethenyl]cyclopropyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC(C2(CC2)C(=C)C=2C(=CC(Cl)=CC=2)Cl)=C1 WQRNMNNPLNYLFU-UHFFFAOYSA-N 0.000 claims description 4
- WTLZQZUZMJQMQH-UHFFFAOYSA-N 3-[1-[1-(2,4-dichlorophenyl)prop-1-enyl]cyclopropyl]pyridine Chemical compound C1CC1(C=1C=NC=CC=1)C(=CC)C1=CC=C(Cl)C=C1Cl WTLZQZUZMJQMQH-UHFFFAOYSA-N 0.000 claims description 4
- YIGXGTVIWCNZKT-UHFFFAOYSA-N 3-[1-chloro-3-(2,4-dichlorophenyl)but-1-en-2-yl]pyridine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)C(=CCl)C1=CC=CN=C1 YIGXGTVIWCNZKT-UHFFFAOYSA-N 0.000 claims description 4
- HFOZKNMEXBZCNI-UHFFFAOYSA-N 3-[1-chloro-3-(2,4-dichlorophenyl)hex-1-en-5-yn-2-yl]pyridine Chemical compound C=1C=CN=CC=1C(=CCl)C(CC#C)C1=CC=C(Cl)C=C1Cl HFOZKNMEXBZCNI-UHFFFAOYSA-N 0.000 claims description 4
- RRRZUGWXVNQSQP-UHFFFAOYSA-N 3-[3-(2,4-dichlorophenyl)-1-methoxypent-1-en-2-yl]pyridine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CC)C(=COC)C1=CC=CN=C1 RRRZUGWXVNQSQP-UHFFFAOYSA-N 0.000 claims description 4
- YXQQGQDVMMJKIG-UHFFFAOYSA-N 3-[4-(2,4-dichlorophenyl)non-5-en-1-yn-5-yl]pyridine Chemical compound C=1C=CN=CC=1C(=CCCC)C(CC#C)C1=CC=C(Cl)C=C1Cl YXQQGQDVMMJKIG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- SFIPCAMAJJDDNT-UHFFFAOYSA-N 3-[3-(2,4-dichlorophenyl)-1-methoxybut-1-en-2-yl]pyridine Chemical compound C=1C=CN=CC=1C(=COC)C(C)C1=CC=C(Cl)C=C1Cl SFIPCAMAJJDDNT-UHFFFAOYSA-N 0.000 claims description 3
- UPFIGHANQXFCEI-UHFFFAOYSA-N 3-[3-(2,4-dichlorophenyl)hex-1-en-2-yl]pyridine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)C(=C)C1=CC=CN=C1 UPFIGHANQXFCEI-UHFFFAOYSA-N 0.000 claims description 3
- WWYLJYWCQUFKHG-UHFFFAOYSA-N 3-[3-(2,4-dichlorophenyl)hex-1-en-5-yn-2-yl]pyridine Chemical compound ClC1=CC(Cl)=CC=C1C(CC#C)C(=C)C1=CC=CN=C1 WWYLJYWCQUFKHG-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 abstract description 22
- 239000000126 substance Substances 0.000 abstract description 18
- -1 N-amino salts Chemical class 0.000 abstract description 12
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 150000001879 copper Chemical class 0.000 abstract description 6
- 239000003921 oil Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 239000002612 dispersion medium Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YXMOPHLAPFSRTI-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-pyridin-3-ylpropan-1-one Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)C(=O)C1=CC=CN=C1 YXMOPHLAPFSRTI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- NNNMNQZTPMMKQD-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-pyridin-3-ylpent-4-yn-1-one Chemical compound ClC1=CC(Cl)=CC=C1C(CC#C)C(=O)C1=CC=CN=C1 NNNMNQZTPMMKQD-UHFFFAOYSA-N 0.000 description 5
- KFRSJYKCHPNRAU-UHFFFAOYSA-N 3-[2-(2,4-dichlorophenyl)hex-3-en-3-yl]pyridine Chemical compound C=1C=CN=CC=1C(=CCC)C(C)C1=CC=C(Cl)C=C1Cl KFRSJYKCHPNRAU-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- UWLXWSXZCPCYJL-UHFFFAOYSA-N (2,4-dichlorophenyl)-(1-pyridin-3-ylcyclopropyl)methanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1(C=2C=NC=CC=2)CC1 UWLXWSXZCPCYJL-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 230000003032 phytopathogenic effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- CGZQCZNRBCLEOH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-pyridin-3-ylethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CC1=CC=CN=C1 CGZQCZNRBCLEOH-UHFFFAOYSA-N 0.000 description 2
- DYHXQEQHRJSNKY-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-methyl-1-pyridin-3-ylpropan-1-one Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)(C)C(=O)C1=CC=CN=C1 DYHXQEQHRJSNKY-UHFFFAOYSA-N 0.000 description 2
- NFHKCEKLBGTYMZ-UHFFFAOYSA-N 3-[4-(2,4-dichlorophenyl)pent-2-en-3-yl]pyridine Chemical compound C=1C=CN=CC=1C(=CC)C(C)C1=CC=C(Cl)C=C1Cl NFHKCEKLBGTYMZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 2
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- SXYFAZGVNNYGJQ-UHFFFAOYSA-M chloromethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCl)C1=CC=CC=C1 SXYFAZGVNNYGJQ-UHFFFAOYSA-M 0.000 description 2
- 229960004106 citric acid Drugs 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 229960000448 lactic acid Drugs 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000001117 sulphuric acid Chemical class 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VFOKYTYWXOYPOX-RVDMUPIBSA-N (z)-2,3-diphenylprop-2-enenitrile Chemical class C=1C=CC=CC=1C(/C#N)=C/C1=CC=CC=C1 VFOKYTYWXOYPOX-RVDMUPIBSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FVZKNLOVJGXZMY-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-methyl-2-pyridin-3-ylpropan-1-one Chemical compound C=1C=CN=CC=1C(C)(C)C(=O)C1=CC=C(Cl)C=C1Cl FVZKNLOVJGXZMY-UHFFFAOYSA-N 0.000 description 1
- ZDQWEDFCHIQNIJ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-pyridin-3-ylbutan-1-one Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CC)C(=O)C1=CC=CN=C1 ZDQWEDFCHIQNIJ-UHFFFAOYSA-N 0.000 description 1
- PIODTJOXJJOIIK-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-pyridin-3-ylethanone Chemical compound ClC1=CC(Cl)=CC=C1CC(=O)C1=CC=CN=C1 PIODTJOXJJOIIK-UHFFFAOYSA-N 0.000 description 1
- QVDRAGAHRVATHF-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-pyridin-3-ylpentan-1-one Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)C(=O)C1=CC=CN=C1 QVDRAGAHRVATHF-UHFFFAOYSA-N 0.000 description 1
- JOCCCKOFQRTOIM-UHFFFAOYSA-M 2-chloroethyl(dimethyl)sulfanium;iodide Chemical compound [I-].C[S+](C)CCCl JOCCCKOFQRTOIM-UHFFFAOYSA-M 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- SFIPCAMAJJDDNT-XNTDXEJSSA-N 3-[(e)-3-(2,4-dichlorophenyl)-1-methoxybut-1-en-2-yl]pyridine Chemical compound C=1C=CN=CC=1C(=C/OC)/C(C)C1=CC=C(Cl)C=C1Cl SFIPCAMAJJDDNT-XNTDXEJSSA-N 0.000 description 1
- SFIPCAMAJJDDNT-GDNBJRDFSA-N 3-[(z)-3-(2,4-dichlorophenyl)-1-methoxybut-1-en-2-yl]pyridine Chemical compound C=1C=CN=CC=1C(=C/OC)\C(C)C1=CC=C(Cl)C=C1Cl SFIPCAMAJJDDNT-GDNBJRDFSA-N 0.000 description 1
- DLGBDIJOANAAAT-UHFFFAOYSA-M 3-[1-[1-(2,4-dichlorophenyl)ethenyl]cyclopropyl]pyridin-1-ium-1-amine;2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1.N[N+]1=CC=CC(C2(CC2)C(=C)C=2C(=CC(Cl)=CC=2)Cl)=C1 DLGBDIJOANAAAT-UHFFFAOYSA-M 0.000 description 1
- LXQFVSZJXIBXOU-UHFFFAOYSA-N 3-[3-(2,4-dichlorophenyl)but-1-en-2-yl]-1-oxidopyridin-1-ium Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)C(=C)C1=CC=C[N+]([O-])=C1 LXQFVSZJXIBXOU-UHFFFAOYSA-N 0.000 description 1
- LHZYVYCOFGJRLZ-UHFFFAOYSA-M 3-[3-(2,4-dichlorophenyl)but-1-en-2-yl]pyridin-1-ium-1-amine 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1.C=1C=C(Cl)C=C(Cl)C=1C(C)C(=C)C1=CC=C[N+](N)=C1 LHZYVYCOFGJRLZ-UHFFFAOYSA-M 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000223651 Aureobasidium Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000221866 Ceratocystis Species 0.000 description 1
- 241000221868 Ceratocystis fimbriata Species 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- 241001620052 Cercosporella Species 0.000 description 1
- 241001600093 Coniophora Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241001181537 Hemileia Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000486186 Menticirrhus littoralis Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- NOKCSEDYJVNSDP-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCCCCCCC[Na] NOKCSEDYJVNSDP-UHFFFAOYSA-N 0.000 description 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000221671 Ophiostoma ulmi Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000087479 Pseudocercospora fijiensis Species 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- NWQXYQUFNNDNES-UHFFFAOYSA-N S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)[Na] Chemical compound S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)[Na] NWQXYQUFNNDNES-UHFFFAOYSA-N 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- BIPUHAHGLJKIPK-UHFFFAOYSA-N dicyclopropylmethanone Chemical class C1CC1C(=O)C1CC1 BIPUHAHGLJKIPK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000010695 polyglycol Chemical class 0.000 description 1
- 229920000151 polyglycol Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical class C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Definitions
- the invention concerns new pyridine derivatives of the formula ##STR3## wherein X signifies a group ##STR4## and R 1 , R 2 , R 3 , R 4 and R 5 have the significances given in the description, and their N-oxides, N-amino salts, copper complexes and acid addition salts, processes for the manufacture of these substances, fungicidal compositions which contain these substances as the active ingredient and the use of such substances and compositions for the control of fungi in agriculture and in horticulture.
- the present invention is concerned with heterocyclic compounds, namely pyridine derivatives of the formula ##STR5## wherein X signifies a group (a) or (b) ##STR6## R 1 and R 2 signify methyl or together form ethylene, R 3 signifies hydrogen, chlorine, C 1-4 -alkyl or methoxy,
- R 4 signifies hydrogen or methyl
- R 5 signifies methyl or, where R 4 signifies hydrogen, also C 1-4 -alkyl, allyl or propargyl or
- R 4 and R 5 together form ethylene, as well as the N-oxides, N-amino salts and copper complexes of the compounds of formula I and finally the acid addition salts of the compounds of formula I and of their N-oxides.
- the invention is also concerned with a process for the manufacture of the compounds in accordance with the invention, fungicidal compositions which contain such compounds as the active ingredient as well as the use of such compounds and compositions for the control of fungi in agriculture and in horticulture.
- N-amino salts there are to be understood the compounds of formula I in which the 3-pyridyl group is modified in accordance with the following formula: ##STR7## wherein (A 1 ).sup. ⁇ signifies the anion of a physiologically compatible acid.
- Examples of-such acids are alkanecarboxylic acids, benzoic acid and it nuclear-substituted derivatives such as, for example, alkyl-, nitro- and/or chloro-substituted benzoic acids, optionally substituted benzenesulphonic acid; carbamic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid and sulphuric acid.
- physiologically compatible salts there come into consideration physiologically compatible salts.
- these compounds with inorganic and organic acids such as hydrochloric acid; nitric acid; phosphoric acid; mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid; and sulphonic acids, e.g. 1, 5-naphthalene-disulphonic acid.
- inorganic and organic acids such as hydrochloric acid; nitric acid; phosphoric acid; mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid
- sulphonic acids e.g. 1, 5-naphthalene-disulphonic acid.
- the N-oxides of the compounds of formula I can also form salts with suitable acids.
- suitable acids e.g. physiologically compatible salts, preferably salts with strong acids such as inorganic acids, e.g. hydrochloric acid, nitric acid and phosphoric acid, and sulphonic acids, e.g. 1, 5-naphthalene-disulphonic acid.
- copper complexes there are meant especially copper(II) complexes of the formula ##STR8## in which A 2 signifies the anion of an organic or inorganic acid such as formic acid, acetic acid, propionic acid, benzoic acid, oxalic acid, tartaric acid, lactic acid, salicylic acid, citric acid, carbonic acid, sulphuric acid, nitric acid or hydrochloric acid.
- a 2 preferably signifies acetate.
- the compounds can be present as E- and Z-isomers and/or as atropic isomers.
- Formula I is intended to embrace all of these possible isomeric forms and their mixtures.
- R 1 and R 2 in formula I together signify ethylene.
- R 3 preferably signifies hydrogen or methoxy
- R 4 preferably signifies hydrogen
- R 5 preferably signifies methyl.
- the process in accordance with the invention for the manufacture of the compounds in accordance with the invention comprises a) reacting a ketone of the formula ##STR9## wherein Y signifies a group (a') or (b') ##STR10## and R 1 , R 2 , R 4 and R 5 have the significances given above, with a triphenylphosphonium salt of the formula
- R 3 has the significance given above and Hal ⁇ signifies a chloride or bromide ion
- A3 signifies the residue of a physiologically compatible acid
- a 2 has the significance given above.
- Process variant a) is conveniently carried out by suspending a triphenylphosphonium salt of formula III in an inert diluent such as an aromatic hydrocarbon, e.g. benzene or toluene, an aliphatic or cyclic ether, e.g. 1, 2-dimethoxyethane, tetrahydrofuran or dioxan, or a dialkylamide, e.g. dimethylformamide, and reacting with a base such as an alkali metal hydride, e.g. sodium hydride, an alkali metal alcoholate, e.g. sodium methylate or potassium tert.butylate, an alkali metal amide, e.g.
- an inert diluent such as an aromatic hydrocarbon, e.g. benzene or toluene, an aliphatic or cyclic ether, e.g. 1, 2-dimethoxyethane, tetrahydrofuran
- N-oxide formation according to process variant (b) is conveniently effected under those reaction conditions which are described in European Patent Specification No. 74018, page 5, lines 47-61, for the N-oxidation of pyridine and pyrazine derivatives.
- N-amination of a compound of formula I with an amine derivative of formula IV is conveniently carried out by treating the compound I with the amine derivative in an inert organic diluent such as a halogenated aliphatic hydrocarbon, e.g. methylene chloride or chloroform, at temperatures between 0° C. and the reflux temperature of the reaction mixture.
- an inert organic diluent such as a halogenated aliphatic hydrocarbon, e.g. methylene chloride or chloroform
- the compounds I or their N-oxides are reacted with the desired acids in the usual manner.
- Process variant (d) is conveniently carried out by stirring together intensively a solution of the compound of formula I in an inert water-immiscible diluent such as a halogenated aliphatic hydrocarbon, e.g. methylene chloride or chloroform, and an aqueous solution of the copper salt of formula V.
- an inert water-immiscible diluent such as a halogenated aliphatic hydrocarbon, e.g. methylene chloride or chloroform
- ketones of general formula II which are used as starting materials in process variant a) are either known or can be produced according to methods known per se [see e.g. European Patent Publications Nos. 74018 and 117485 as well as--in the case of the production of the cyclopropyl ketones of formula II (R 1 and R 2 or R 4 and R 5 together signify ethylene)--Tetrahedron Letters, 25, 5501 (1984)].
- the reagents of formulae III and IV are known and can be produced according to known methods.
- the compounds in accordance with the invention possess fungicidal activity and can accordingly be used for the control of fungi in agriculture, in horticulture as well as in the processing of wood. They are especially suitable for inhibiting the growth of phytopathogenic fungi or for destroying phytopathogenic fungi on parts of plants, e.g. leaves, stems, roots, bulbs, tubers, fruits or flowers, and on seeds as well as in soil. Further, fungi which destroy and discolour wood can be controlled with the compounds in accordance with the invention.
- the compounds in accordance with the invention are especially effective in the control of fungi of the classes Deuteromycetes, Ascomycetes and Basidiomycetes such as, for example, Botrytis cinerea, Erysiphe cichoracearum, Erysiphe graminis, Uncinula necator, Podosphaera leucotricha, Venturia inaequalis, Cercospora archidicola, Cercospora beticola and Mycosphaerella fijiensis as well as of harmful fungi of the genera Sphaerotheca, Puccinia, Uromyces, Hemileia, Rhizoctonia, Alternaria, Cercosporella, Ceratocystis (e.g.
- Ceratocystis ulmi and Ceratocystis fimbriata Verticillium, Fusarium, Helmithosporium, Sclerotinia, Penicillium, Septona, Ustilago, Tilletia, Coniophora, Cloeophyllum and Aureobasidium.
- the compounds in accordance with the invention are distinguished by local and/or systemic activity.
- the compounds in accordance with the invention are active against phytopathogenic fungi under greenhouse conditions even at concentrations of 1 mg to 500 mg of active ingredient per liter of spray liquor. In the open, concentrations of 25 g to 1500 g of active ingredient of formula I per hectare and treatment are advantageously used. For the control of seed-borne or soil-borne fungi in a dressing process there are advantageously used 0.05 g to 1.5 g of active ingredient of formula I per kg of seeds.
- the above-mentioned starting materials of general formula II are also valuable as fungicides, since they have a similar spectrum of activity to the compounds of formula I. These starting materials can accordingly also be used for the control of fungi in agriculture and in horticulture, namely in the same manner as the compounds in accordance with the invention.
- compositions e.g. solutions, suspensions, emulsions, emulsifiable concentrates and pulverous preparations.
- the fungicidal compositions in accordance with the invention contain an effective amount of at least one compound of general formula I, as defined above, or of a N-oxide, N-amino salt, acid addition salt or copper complex of such a compound as well as formulation adjuvants.
- the compositions conveniently contain at least one of the following formulation adjuvants:
- Solid carrier substances solvents or dispersion media; tensides (wetting and emulsifying agents); dispersing agents (without tenside action); and stabilizers.
- solid carrier substances there essentially come into consideration: natural mineral substances such as kaolin, aluminas, siliceous earth, talc, bentonite, chalk, e.g. whiting, magnesium carbonate, limestone, quartz, dolomite, attapulgite, montmorillonite and diatomaceous earth; synthetic mineral substances such as highly dispersible silicic acid, aluminium oxide and silicates; organic substances such as cellulose, starch, urea and synthetic resins; and fertilizers such as phosphates and nitrates, whereby such carrier substances can be present e.g. as granulates or powders.
- natural mineral substances such as kaolin, aluminas, siliceous earth, talc, bentonite, chalk, e.g. whiting, magnesium carbonate, limestone, quartz, dolomite, attapulgite, montmorillonite and diatomaceous earth
- synthetic mineral substances such as highly dispersible silicic acid, aluminium oxide and silicates
- aromatics such as toluene, xylenes, benzene and alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes and methylene chloride; aliphatic hydrocarbons such as cyclohexane and paraffins, e.g.
- solvents or dispersion media such as dimethylformamide, N-methylpyrrolidone and dimethyl sulphoxide, such solvents or dispersion media preferably having flash points of at least 30° C. and boiling Points of at least 50° C, and water.
- solvents or dispersion media there also come into consideration so-called liquified gaseous extenders or carrier substances, these being products which are gaseous at room temperature and under normal pressure. Examples of such products are especially aerosol propellants such as halogenated hydrocarbons, e.g. dichlorodifluoromethane.
- organic solvents can e.g. also be used as auxiliary solvents.
- the tensides can be non-ionic compounds such as condensation products or fatty acids, fatty alcohols or fatty-substituted phenols with ethylene oxide; fatty acid esters and ethers of sugars or polyvalent alcohols; the products which are obtained from sugars or polyvalent alcohols by condensation with ethylene oxide; block polymers of ethylene oxide and propylene oxide; or alkyldimethylamine oxides.
- the tensides can also be anionic compounds such as soaps; fatty sulphate esters, e.g. dodecyl sodium sulphate, octadecyl sodium sulphate and cetyl sodium sulphate; alkyl sulphonates, aryl sulphonates and fatty-aromatic sulphonates such as alkylbenzenesulphonates, e.g. calcium dodecylbenzenesulphonate, and butylnaphthalene sulphonates; and more complex fatty sulphonates, e.g. the amide condensation products of oleic acid and N-methyltaurine and the sodium sulphonate of dioctyl succinate.
- fatty sulphate esters e.g. dodecyl sodium sulphate, octadecyl sodium sulphate and cetyl sodium sulphate
- the tensides can be cationic compounds such as alkyldimethylbenzylammonium chlorides, dialkyldimethylammonium chlorides, alkyltrimethylammonium chlorides and ethoxylated quaternary ammonium chlorides.
- dispersing agents without tenside activity
- lignin sodium and ammonium salts of lignin sulphonic acids, sodium salts of maleic anhydride-diisobutylene copolymers, sodium and ammonium salts of sulphonated polycondensation products of naphthalene and formaldehyde, and sulphite lyes.
- dispersing agents which are especially suitable as thickening or anti-settling agents, there can be used e.g. methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, polyvinyl alcohol, alginates, caseinates and blood albumin.
- Suitable stabilizers are acid-binding agents, e.g. epichlorohydrin, phenyl glycidyl ether and soya epoxides; antioxidants, e.g. gallic acid esters and butylhydroxytoluene; UV-absorbers, e.g. substituted benzophenones, diphenylacrylonitrile acid esters and cinnamic acid esters; and deactivators, e.g. salts of ethylenediaminetetraacetic acid and polyglycols.
- acid-binding agents e.g. epichlorohydrin, phenyl glycidyl ether and soya epoxides
- antioxidants e.g. gallic acid esters and butylhydroxytoluene
- UV-absorbers e.g. substituted benzophenones, diphenylacrylonitrile acid esters and cinnamic acid esters
- the fungicidal compositions in accordance with the invention can contain, in addition to the active ingredients of formula I, other active ingredients, e.g. other fungicidal agents, insecticidal and acaricidal agents, bactericides, plant growth regulators and fertilizers.
- active ingredients e.g. other fungicidal agents, insecticidal and acaricidal agents, bactericides, plant growth regulators and fertilizers.
- Such combination compositions are suitable for broadening the spectrum of activity or for specifically influencing the plant growth.
- the fungicidal compositions in accordance with the invention generally contain, according to type, between 0.0001 and 95 weight percent of compound in accordance with the invention or compounds in accordance with the invention as the active ingredient(s). They can be present in a form which is suitable for storage and transport. In such forms, e.g. emulsifiable concentrates, the active ingredient concentration is normally in the higher region of the above concentration range. These forms can be diluted with the same or different formulation adjuvants to give active ingredient concentrations which are suitable for practical use and such concentrations normally lie in the lower region of the above concentration range.
- Emulsifiable concentrates generally contain 5 to 95 weight percent, preferably 25 to 75 weight percent, of the compound or compounds of formula I.
- spray liquors there can be present e.g. concentrations between 0.0001 and 20 weight percent.
- spray liquors formulated in which the active ingredient concentration is preferably from 0.5 to 20 weight percent while the spray liquors formulated in the Low-Volume process and in the High-Volume process preferably have an active ingredient concentration of 0.02 to 1.0 and 0.002 to 0.1 weight percent, respectively.
- the fungicidal compositions in accordance with the invention can be manufactured by mixing at least one compound in accordance with the invention with formulation adjuvants.
- compositions can be carried out in a known manner, e.g. by mixing the active ingredient with solid carrier substances, by dissolution or suspension in suitable solvents or dispersion media, if necessary with the use of tensides as wetting or emulsifying agents or of dispersing agents, by diluting Pre-prepared emulsifiable concentrates with solvents or dispersion media etc.
- the active ingredient can be mixed with a solid carrier substance, e.g. by grinding them together; or the solid carrier substance can be impregnated with a solution or suspension of the active ingredient and then the solvent or dispersion medium can be removed by evaporation, heating or by sucking-off under reduced pressure.
- a solid carrier substance e.g. by grinding them together; or the solid carrier substance can be impregnated with a solution or suspension of the active ingredient and then the solvent or dispersion medium can be removed by evaporation, heating or by sucking-off under reduced pressure.
- tensides or dispersing agents such pulverous compositions can be made readily wettable with water, so that they can be converted into aqueous suspensions which are suitable e.g. as spray compositions.
- the compounds in accordance with the invention can also be mixed with a tenside and a solid carrier substance to form a wettable powder which is dispersible in water or they can be mixed with a solid pre-granulated carrier substance to form a product in the form of a granulate.
- a compound in accordance with the invention can be dissolved in a water-immiscible solvent such as, for example, an alicyclic ketone, which conveniently contains dissolved emulsifying agent, so that the solution becomes self-emulsifying upon addition to water.
- a water-immiscible solvent such as, for example, an alicyclic ketone, which conveniently contains dissolved emulsifying agent, so that the solution becomes self-emulsifying upon addition to water.
- the active ingredient can be mixed with an emulsifying agent and the mixture can then be diluted with water to the desired concentration.
- the active ingredient can be dissolved in a solvent and thereafter the solution can be mixed with an emulsifying agent.
- Such a mixture can likewise be diluted with water to the desired concentration. In this manner there are obtained emulsifiable concentrates or ready-for-use emulsions.
- compositions in accordance with the invention can be carried out according to the application methods which are usual in plant protection or in agriculture.
- the method in accordance with the invention for the control of fungi comprises treating the locus to be protected, e.g. plants, parts of plants or seeds, with an effective amount of a compound in accordance with the invention or of a composition in accordance with the invention.
- the mixture is left to come to room temperature during about 16 hours, poured on to ice-water and extracted three times with 100 ml of methylene chloride each time. After washing with water and distilling off the solvent under reduced pressure the residue is chromatographed on silica gel with diethyl ether as the eluent. The product is crystallized from n-hexane and there are thus obtained 15 g of 4'-dichloro-2-methyl-2-(3-pyridyl)-propiophenone as beige crystals, m.p. 75-76° C.
- An emulsifiable concentrate has the following composition
- the active ingredient and the emulsifiers are taken up in the solvent.
- a ready-for-use spray liquor of any desired concentration can be manufactured by emulsifying this concentrate.
- a seed dressing composition has the following composition:
- the components are mixed with one another and the mixture is ground finely in a suitable mill.
- the composition can be mixed directly in the dry state with the seeds or, by the addition of water, can be converted firstly into a flowable slurry which can then be distributed on the seeds.
- a spray powder has the following composition:
- the components are mixed with one another and the mixture is ground finely in a suitable mill.
- a ready-for-use spray liquor is obtained by dispersing the mixture in water.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH747/89 | 1989-03-01 | ||
CH74789 | 1989-03-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
US5036074A true US5036074A (en) | 1991-07-30 |
Family
ID=4194258
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/481,264 Expired - Fee Related US5036074A (en) | 1989-03-01 | 1990-02-20 | Certain 2,4-dichloro-phenyl(loweralkylidene) pyridines having fungicidal activity |
Country Status (9)
Country | Link |
---|---|
US (1) | US5036074A (fr) |
EP (1) | EP0385267A3 (fr) |
JP (1) | JPH02275856A (fr) |
KR (1) | KR900014318A (fr) |
AU (1) | AU638434B2 (fr) |
BR (1) | BR9000897A (fr) |
HU (1) | HU207044B (fr) |
PT (1) | PT93310B (fr) |
ZA (1) | ZA901358B (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5175167A (en) * | 1990-02-09 | 1992-12-29 | Basf Aktiengesellschaft | Hetarylalkenes, their preparation and intermediates for their preparation and their use |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3914820A1 (de) * | 1989-05-05 | 1990-11-08 | Basf Ag | Neue pyridinderivate und ihre verwendung als fungizide |
US5360459A (en) | 1991-05-13 | 1994-11-01 | The Lubrizol Corporation | Copper-containing organometallic complexes and concentrates and diesel fuels containing same |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1225092A (fr) * | 1980-10-10 | 1987-08-04 | Franz Dorn | Derives de pyridine et de pyrazine |
AU554104B2 (en) * | 1981-09-01 | 1986-08-07 | F. Hoffmann-La Roche Ag | Heterocyclic compounds and fungicides containing same |
CA1234388A (fr) * | 1982-09-27 | 1988-03-22 | Pieter T. Haken | Composes fongicides contenant des derives de l'ethene |
EP0117485A3 (fr) * | 1983-02-28 | 1985-01-23 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Dérivés de pyridine, pyrazine et pyrimidine et leur utilisation comme agents fongicides |
DK429884A (da) * | 1983-10-07 | 1985-04-08 | Hoffmann La Roche | Heterocycliske forbindelser |
JPS62169766A (ja) * | 1986-01-23 | 1987-07-25 | Ishihara Sangyo Kaisha Ltd | ピリジン系化合物及びそれらを含有する有害生物防除剤 |
GB8605281D0 (en) * | 1986-03-04 | 1986-04-09 | Ici Plc | Diphenyl ether derivatives |
DE4018260A1 (de) * | 1990-06-07 | 1991-12-12 | Basf Ag | Derivate des (beta)-picolins und diese enthaltende pflanzenschutzmittel |
-
1990
- 1990-02-20 US US07/481,264 patent/US5036074A/en not_active Expired - Fee Related
- 1990-02-21 AU AU50032/90A patent/AU638434B2/en not_active Ceased
- 1990-02-22 EP EP19900103432 patent/EP0385267A3/fr not_active Ceased
- 1990-02-22 ZA ZA901358A patent/ZA901358B/xx unknown
- 1990-02-23 BR BR909000897A patent/BR9000897A/pt not_active Application Discontinuation
- 1990-02-26 HU HU901038A patent/HU207044B/hu not_active IP Right Cessation
- 1990-02-27 KR KR1019900002482A patent/KR900014318A/ko not_active Application Discontinuation
- 1990-03-01 JP JP2047380A patent/JPH02275856A/ja active Pending
- 1990-03-01 PT PT93310A patent/PT93310B/pt not_active IP Right Cessation
Non-Patent Citations (2)
Title |
---|
Fieser and Fieser "Reagents for Organic Synthesis", vol. 6, p. 647, Wiley-Interscience publishers QD 262 FS (1977). |
Fieser and Fieser Reagents for Organic Synthesis , vol. 6, p. 647, Wiley Interscience publishers QD 262 FS (1977). * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5175167A (en) * | 1990-02-09 | 1992-12-29 | Basf Aktiengesellschaft | Hetarylalkenes, their preparation and intermediates for their preparation and their use |
Also Published As
Publication number | Publication date |
---|---|
AU5003290A (en) | 1990-09-06 |
HU901038D0 (en) | 1990-05-28 |
HUT53874A (en) | 1990-12-28 |
EP0385267A2 (fr) | 1990-09-05 |
PT93310A (pt) | 1990-11-07 |
HU207044B (en) | 1993-03-01 |
PT93310B (pt) | 1996-01-31 |
BR9000897A (pt) | 1991-02-13 |
JPH02275856A (ja) | 1990-11-09 |
AU638434B2 (en) | 1993-07-01 |
KR900014318A (ko) | 1990-10-23 |
ZA901358B (en) | 1990-11-28 |
EP0385267A3 (fr) | 1991-09-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4548945A (en) | Fungicidally active substituted 1-hydroxyethyl-triazolyl derivatives | |
US4753947A (en) | Certain fungicidal alphabenzyl-3-pyridylmethanol, the corresponding chloro derivatives thereof or the N-oxides thereof | |
US4495191A (en) | Fungicidal 3-1,2,4-triazol-1-yl-1,2-diaryl-1-halogeno-prop-1-ene derivatives, compositions, and method of use | |
US4699652A (en) | Fungicidal pyridine derivatives for use in agriculture | |
US4505922A (en) | Triazolealkynol fungicidal agents | |
KR880002228B1 (ko) | 피리딘카비놀의 제조방법 | |
US4102891A (en) | 1-(2-Halogeno-2-phenyl-ethyl)-triazoles | |
NZ207229A (en) | Pyridine,pyrazine and pyrimidine derivatives and fungicidal compositions | |
CA1150279A (fr) | Derives de triazolyl-alcene; methode de preparation et emploi comme fongicides | |
US4154842A (en) | Fungicidally and bactericidally active 1-azolyl-4-hydroxy-1-phenoxy-butane derivatives | |
HU192005B (en) | Fungicide composition and process for preparing azolyl-3-pyrazolyl-2-propanol derivatives | |
US5036074A (en) | Certain 2,4-dichloro-phenyl(loweralkylidene) pyridines having fungicidal activity | |
US4380544A (en) | 1,3-Dioxolane compounds and their use as fungicides | |
US4622334A (en) | Combating fungi with 3-cycloalkyl-1-(1,3-dioxan-5-yl)2-(1,2,4-triazol-1-yl)-propan-1-ones and propan-1-ols | |
JPS60224689A (ja) | (1,2,4‐トリアゾル‐1‐イル)‐メチル‐カルビノール | |
US4771065A (en) | Fungicidal novel substituted phenethyl-triazolyl derivatives | |
US4360529A (en) | Combating fungi with trisubstituted benzyl oxime ethers | |
GB2117772A (en) | Heterocyclic oximes | |
US4596815A (en) | Antifungal azolylmethyl-thienyl-carbinol derivatives | |
US4427672A (en) | Combating fungi with substituted triazolylalkyl pyridyl ethers | |
NZ199642A (en) | Imidazole and triazole-substituted 1,3-dioxolanes and dioxanes | |
US4797412A (en) | Fungicidal substituted cyclopropyl oxime ethers | |
CA1098121A (fr) | Composes de phenylazophenyloxytriazolyle | |
US5219876A (en) | Substituted-cyano-2-[4-(phenyl-ethynyl)phenyl]-1-1 (1H-1,2,4-triazol-1-yl)ethane derivatives | |
US4744817A (en) | Triazole derivatives |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: F. HOFFMANN-LA ROCHE AG, SWITZERLAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:ISENRING, HANS P.;ZEHNDER, BEAT;ZIEGLER, HUGO;REEL/FRAME:005244/0995 Effective date: 19900124 Owner name: HOFFMANN-LA ROCHE INC., NEW JERSEY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:F. HOFFMAN-LA ROCHE AG, 124 GRENZACHERSTRASSE, BASLE, SWITZERLAND, A SWISS COMPANY;REEL/FRAME:005254/0238 Effective date: 19900124 |
|
AS | Assignment |
Owner name: ROCHE HOLDINGS, INC. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:HOFFMANN-LA ROCHE INC.;REEL/FRAME:005557/0142 Effective date: 19901113 |
|
AS | Assignment |
Owner name: CIBA-GEIGY CORPORATION, A CORP. OF NY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:ROCHE HOLDINGS, INC., A CORP. OF DE;REEL/FRAME:005665/0568 Effective date: 19910301 |
|
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 19990730 |
|
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |